Ask HN: Good books on philosophy of engineering?

It' smaybe check out the Computer History Museum.

Read Feynman's (or about) books. "Surely you're joking, Mr Feynman" is light but profound. Max Tegmark's "Our Mathematical Universe" is great. "I am a strange loop" by Douglas Hofstadter will connect many dots. If you want to peek deeper - "Through two doors at once" describes experiments at the edge of our reality. "The singularity is near" is a good perspective that connects dots through time back many years to many in the future.

These are just some incomplete starter points. It's deep, beautiful rabbit hole. Enjoy it.

There is a lot of emphasis on simplicity and that things are the best when they work seamlessly.

Chapter 17, from the translation by Derek Lin, which I wholeheartedly recommend:

    The highest rulers, people do not know they have them
    The next level, people love them and praise them
    The next level, people fear them
    The next level, people despise them